Water → 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide

HRID 2224390ノート

反応式

HRID 2224390 の反応式
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].C(N(CC)CC)C.O>O1CCOCC1>[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 9773Ethanamine, 2,2,2-trifluoro-

生成物 1

HCID 692881143-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide収率 83%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 2,2,2-trifluoroethylamine (1.17 ml, 15 mmol) in dioxane (37 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (3.0 g, 14 mmol) and triethylamine (2.06 ml, 15 mmol). The light yellow suspension was stirred at room temperature for 4 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) to yield 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide (3.18 g, 83%) as a light yellow solid. MS (ISP) 283.9 [(M−H)−].

後処理

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-fababdeaa52c4851a3df810a4461d813
出典データセット
uspto-grants-2008_05
特許番号
US07378417B2

反応ノート

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